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UPS shipping label integration supports Signature Required delivery option as a setting for the shipping method. To set the setting tick Requires Signature next to the mapped shipping service.

Can I configure the system to add Signature Requires for UPS service if an order is of a certain value?

Yes. To set it up you will need to have two postal services setup in Linnworks that map to the same UPS service. One will be with mapped to a UPS service with Requires Signature option turned on and the other without.
When an order is over a certain value, you have to allocate an order to UPS Standard – Signature Requires, otherwise  to UPS Standard. The allocation can be automated through an order macro script.